EP0266848B1 - Ester compound lubricants - Google Patents

Ester compound lubricants Download PDF

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Publication number
EP0266848B1
EP0266848B1 EP87202149A EP87202149A EP0266848B1 EP 0266848 B1 EP0266848 B1 EP 0266848B1 EP 87202149 A EP87202149 A EP 87202149A EP 87202149 A EP87202149 A EP 87202149A EP 0266848 B1 EP0266848 B1 EP 0266848B1
Authority
EP
European Patent Office
Prior art keywords
group
optionally substituted
formula
tractive
mono
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP87202149A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0266848A2 (en
EP0266848A3 (en
Inventor
Martin Philip Dare-Edwards
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shell Internationale Research Maatschappij BV
Original Assignee
Shell Internationale Research Maatschappij BV
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV
Priority to AT87202149T priority Critical patent/ATE60876T1/de
Publication of EP0266848A2 publication Critical patent/EP0266848A2/en
Publication of EP0266848A3 publication Critical patent/EP0266848A3/en
Application granted granted Critical
Publication of EP0266848B1 publication Critical patent/EP0266848B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—Esters
    • C10M105/42—Complex esters, i.e. compounds containing at least three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compound: monohydroxy compounds, polyhydroxy compounds, monocarboxylic acids, polycarboxylic acids and hydroxy carboxylic acids
    • C10M105/46—Complex esters, i.e. compounds containing at least three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compound: monohydroxy compounds, polyhydroxy compounds, monocarboxylic acids, polycarboxylic acids and hydroxy carboxylic acids derived from the combination of monohydroxy compounds, dihydroxy compounds and dicarboxylic acids only and having no free hydroxy or carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—Esters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—Esters
    • C10M105/34—Esters of monocarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—Esters
    • C10M105/36—Esters of polycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—Esters
    • C10M105/38—Esters of polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/286—Esters of polymerised unsaturated acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
    • C10M2207/304—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monohydroxy compounds, dihydroxy compounds and dicarboxylic acids only and having no free hydroxy or carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/042—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for automatic transmissions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/044—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for manual transmissions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/046—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for traction drives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids

Definitions

  • the present process relates to the use of certain ester compounds as lubricants, in particular their use in tractive drives.
  • tractive drives can be used in a variety of engineering applications, being of particular value in tractive drives.
  • Traction is broadly defined as the adhesive friction of a body on a surface on which it moves.
  • a tractive drive is a device in which torque is transmitted from an input element to an output element through nominal point or line contact typically with a rolling action by virtue of the traction between the contacting elements. While tractive elements are commonly spoken of as being in contact, it is generally accepted that a fluid film is present therebetween. Almost all tractive drives require fluids to remove heat, to prevent wear at the contact surfaces and to lubricate bearings and other moving parts associated with the drive. Thus, instead of metal to metal rolling contact there is a film of fluid introduced into the contact zone and interposed between the metal elements.
  • tractive drives are designed to operate with a tractive fluid which preferably has a coefficient of traction above about 0.06, a viscosity in the range of about 4-20,000 mPas over a temperature range of 40°C to -20°C and good thermal and oxidative stability.
  • the fluid should also be noncorrosive to common materials of construction and have good load-bearing and low wear-rate properties.
  • Mineral base oils are rather unsatisfactory lubricants for tractive drives since in general their traction (friction) coefficient is low, which means that for any given load applied to the gears the maximal tangential force that may be transmitted by the friction wheels is low.
  • esters are those of the general formula where R is a bivalent aliphatic hydrocarbon radical, such as methylene, polymethylene, ethylidine, propylidine, methyl dimethylene butenylidine and the like; R1 and R2 are hydrocarbon radicals such as branched chain alkyl, alkaryl, and cyclo alkyl radicals of which secondary butyl, benzal, cyclohexanol and secondary octyl phenyl are representative. These esters may contain additional substituents or functional groups such as Cl, Br, NH2, NHR, NR1R2, CHO, CO, SH, SR, RSSR, ROR, RO metal.
  • R is a bivalent aliphatic hydrocarbon radical, such as methylene, polymethylene, ethylidine, propylidine, methyl dimethylene butenylidine and the like
  • R1 and R2 are hydrocarbon radicals such as branched chain alkyl, alkaryl, and cyclo al
  • ester compounds constitute excellent traction fluids. Accordingly, the present invention provides the use as traction fluids of ester compounds of the general formula I wherein R1 and R2 are the same and each represents a cyclohexyl group optionally bearing one or more methyl substituents, and R is a methylene, ethylene, vinylene or trimethylene group, which group may contain one or more methyl substituents.
  • Preferred individual compounds are biscyclohexyl malonate, succinate or glutarate, in which the cyclohexyl moieties or the malonate, succinate or glutarate groups may contain one or more methyl substituents, since these compounds have very high traction coefficients.
  • the viscosity characteristics of the above ester compounds are very suitable for use in e.g. friction wheel gears (tractive drives) in which application they may be admixed with conventional grease thickeners.
  • Such thickeners can be of any number of materials commonly used to thicken mineral oils to lubricating viscosity, including both organic and inorganic compositions such as metallic soaps, synthetic polymers, organosiloxanes, clays, bentonite, and colloidal silica.
  • the viscosity properties of compounds to be used in tractive drives are such that the compounds are operable between -30 and 150°C and have a viscosity of at most 250mm2/s at 40°C and at least 3mm 2 /s at 100°C.
  • the compounds show excellent lubricating performance in tractive drives, so the invention provides the use of these ester compounds as traction fluids, and also operation of a tractive drive wherein such esters form the tractive fluid.
  • ester compounds of the present invention can be used per se as traction fluids. They can be mixed with lubricants such as mineral or synthetic oils, and various additives can be added to the ester compounds, such as VI-improvers, pour point depressants, dispersants, detergents, anti-oxidants and the like.
  • the acids (7 mol) were refluxed with the appropriate alcohol (14 mol) in a toluene (1L) mixture and in the presence of p-toluene sulphonic acid (18.0g).
  • the molar ratio acid:alcohol was 1:2.
  • the water formed was collected in a Dean and Stark trap and the reaction was continued until no more water was produced (14 hours).
  • the solution was then cooled and washed firstly with a saturated sodium bicarbonate solution and then by a saturated sodium chloride solution.
  • the crude product was distilled under reduced pressure.
  • the measuring device is a gear dynamometer with a pendulum which is swung out of its vertical balanced position when power is transmitted, the sine of the angle of inclination being a measure of the torque.
  • the torque measurement is pre-calibrated through the design and dimensions of the instrument.
  • the friction coefficient is defined by the torque measured divided by the product of the radial force times the radius of the lower disc.
  • Both discs used had a diameter of 50.0mm, the upper disc having a width of 3mm, the lower one having a width of 10mm.
  • the top shaft speed was 606rpm, and the mean tangential (or surface) velocity was 1.48 ms -1
  • the slip employed was 9.1%.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Lubricants (AREA)
EP87202149A 1986-11-06 1987-11-04 Ester compound lubricants Expired - Lifetime EP0266848B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT87202149T ATE60876T1 (de) 1986-11-06 1987-11-04 Esterzusammensetzung als schmiermittel.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB8626510 1986-11-06
GB868626510A GB8626510D0 (en) 1986-11-06 1986-11-06 Ester compounds as lubricants

Publications (3)

Publication Number Publication Date
EP0266848A2 EP0266848A2 (en) 1988-05-11
EP0266848A3 EP0266848A3 (en) 1988-10-05
EP0266848B1 true EP0266848B1 (en) 1991-02-13

Family

ID=10606881

Family Applications (1)

Application Number Title Priority Date Filing Date
EP87202149A Expired - Lifetime EP0266848B1 (en) 1986-11-06 1987-11-04 Ester compound lubricants

Country Status (16)

Country Link
US (1) US4786427A (ko)
EP (1) EP0266848B1 (ko)
JP (1) JPS63139150A (ko)
KR (1) KR950014392B1 (ko)
CN (1) CN1017156B (ko)
AT (1) ATE60876T1 (ko)
AU (1) AU598315B2 (ko)
BR (1) BR8705936A (ko)
CA (1) CA1291984C (ko)
DE (1) DE3768024D1 (ko)
ES (1) ES2021021B3 (ko)
FI (1) FI91881C (ko)
GB (1) GB8626510D0 (ko)
GR (1) GR3001748T3 (ko)
PT (1) PT86073B (ko)
ZA (1) ZA878273B (ko)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2618271B2 (ja) * 1989-04-26 1997-06-11 日本化薬株式会社 モノｐ―ニトロベンジルマロネートマグネシウム塩の結晶変態及びその製法
AU3321093A (en) * 1991-12-19 1993-07-19 Exxon Research And Engineering Company Refrigeration working fluid
US5306851A (en) * 1992-11-23 1994-04-26 Mobil Oil Corporation High viscosity index lubricant fluid
US5318711A (en) * 1993-01-21 1994-06-07 Quaker Chemical Corporation Method for lubricating metal-metal contact systems in metalworking operations with cyclohexyl esters
US5397488A (en) * 1993-12-09 1995-03-14 Mobil Oil Corporation Oxidatively stable esters derived from diamondoids totally hydroxylated at the bridgeheads
CN1037275C (zh) * 1994-11-11 1998-02-04 西安近代化学研究所 聚氯乙烯用外润滑剂
WO1997021792A1 (fr) * 1995-12-12 1997-06-19 New Japan Chemical Co., Ltd. Huile lubrifiante
US6068918A (en) * 1996-10-15 2000-05-30 N.V. Bekhaert S.A. Steel cord treated with a corrosion inhibiting composition
US5998340A (en) * 1997-03-07 1999-12-07 Hitachi Maxell, Ltd. Lubricant and magnetic recording medium using the same
EP0949319A3 (en) * 1998-04-08 2001-03-21 Nippon Mitsubishi Oil Corporation Traction drive fluid
US6797680B2 (en) * 2003-02-05 2004-09-28 General Motors Corporation Traction fluid with di-acid ester bridged dimer
US6828283B2 (en) 2003-02-05 2004-12-07 Genberal Motors Corporation Traction fluid with alkane bridged dimer
DE10343623A1 (de) * 2003-09-20 2005-04-28 Celanese Chem Europe Gmbh Carbonsäureester auf Basis von Limonanalkohol [3-(4'-Methylcyclohexyl)butanol] mit niedrigem Stockpunkt
JP4938250B2 (ja) * 2005-04-28 2012-05-23 出光興産株式会社 動力伝達用潤滑剤
US8586519B2 (en) * 2007-02-12 2013-11-19 Chevron U.S.A. Inc. Multi-grade engine oil formulations comprising a bio-derived ester component
US20110009300A1 (en) 2009-07-07 2011-01-13 Chevron U.S.A. Inc. Synthesis of biolubricant esters from unsaturated fatty acid derivatives
CN104058965B (zh) * 2014-04-16 2015-09-16 上海通快实业有限公司 二聚酸聚酯及其制备方法和用该聚酯制备可降解微量切削油
JP6274326B2 (ja) * 2014-12-08 2018-02-07 新日本理化株式会社 トラクションドライブ用潤滑油基油
JP7242635B2 (ja) * 2018-03-27 2023-03-20 出光興産株式会社 潤滑油基油、該潤滑油基油を含有する潤滑油組成物、及び該潤滑油組成物を用いた無段変速機
WO2021112946A1 (en) * 2019-12-04 2021-06-10 The Lubrizol Corporation Use of ester base stocks to improve viscosity index and efficiency in driveline and industrial gear lubricating fluids

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2417281A (en) * 1944-11-10 1947-03-11 Standard Oil Dev Co Instrument lubricant
US2817673A (en) * 1952-08-01 1957-12-24 Ruhrchemie Ag Tricyclodecane esters
US2824065A (en) * 1955-05-20 1958-02-18 Sun Oil Co Lithium greases containing naphthenyl diesters
US2849399A (en) * 1956-04-09 1958-08-26 Exxon Research Engineering Co Improved lubricating composition
US3296065A (en) * 1963-10-07 1967-01-03 Monsanto Co Paper products containing carboxylic acid esters and process for preparing such products
US3440894A (en) * 1966-10-13 1969-04-29 Monsanto Co Tractants and method of use
FR2041647A5 (ko) * 1969-05-14 1971-01-29 Inst Francais Du Petrole
US3835050A (en) * 1971-05-13 1974-09-10 Monsanto Co Grease compositions having high tractive coefficients
US3793203A (en) * 1971-05-17 1974-02-19 Sun Oil Co Lubricant comprising gem-structured organo compound
DE2713440A1 (de) * 1977-03-26 1978-09-28 Bayer Ag Carbonsaeureester, deren herstellung und verwendung als basisschmieroel
IT1123575B (it) * 1979-09-10 1986-04-30 Snia Viscosa Esteri di alcoli polivalenti,procedimento per la loro preparazione e loro impiego quali oli lubrificanti
DE3151938A1 (de) * 1981-12-30 1983-07-07 Optimol Oelwerke Gmbh Traktionsfluessigkeit
JPH0631366B2 (ja) * 1986-01-31 1994-04-27 東燃株式会社 トラクシヨンフル−ド
JPS62177099A (ja) * 1987-07-30 1987-08-03 Toa Nenryo Kogyo Kk トラクシヨン用フル−ド

Also Published As

Publication number Publication date
CA1291984C (en) 1991-11-12
ES2021021B3 (es) 1991-10-16
AU598315B2 (en) 1990-06-21
FI874871A (fi) 1988-05-07
ZA878273B (en) 1988-05-03
JPS63139150A (ja) 1988-06-10
DE3768024D1 (de) 1991-03-21
ATE60876T1 (de) 1991-02-15
GB8626510D0 (en) 1986-12-10
FI91881B (fi) 1994-05-13
EP0266848A2 (en) 1988-05-11
KR880006349A (ko) 1988-07-22
EP0266848A3 (en) 1988-10-05
FI874871A0 (fi) 1987-11-04
PT86073B (pt) 1990-11-07
KR950014392B1 (ko) 1995-11-27
CN1017156B (zh) 1992-06-24
PT86073A (en) 1987-12-01
US4786427A (en) 1988-11-22
CN87107642A (zh) 1988-05-18
BR8705936A (pt) 1988-06-14
FI91881C (fi) 1994-08-25
GR3001748T3 (en) 1992-11-23
AU8067287A (en) 1988-08-04

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